Methyl iodide → HCID 20145193, compound

HRID 648658Notes

Reaction equation

HRID 648658 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([C:24]([NH2:26])=[O:25])[C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH3:11])=[C:4]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:3]=1.[H-].[Na+].[CH3:35]I>CN(C)C=O>[CH3:35][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([C:24]([NH2:26])=[O:25])[C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][CH:23]=2)[CH2:9][CH2:10][CH3:11])=[C:4]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20145211HCID 20145211, compound

Product 1

HCID 20145193HCID 20145193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5.0 gm (11.4 m mol) of ethyl 4-[(1-(4-hydroxy-2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzoate in 45 ml of absolute dimethylformamide was added dropwise, under stirring, at ambient temperature, to 548 mg (11.4 m mol) of sodium hydride (50% in oil) in 10 ml of absolute dimethylformamide. The mixture was stirred for a further 15 minutes, and then a solution of 0.71 ml (11.4 m mol) of methyliodide in 8 ml of absolute dimethylformamide was slowly added thereto dropwise. The mixture was stirred for a further two and one-half hours at ambient temperature, evaporated in vacuo, and distributed between water and ether. The ether phase was dried, filtered, and concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel [toluene/acetone (20:1)].

Workup

  1. stirringThe mixture was stirred for a further two and one-half hours at ambient temperature
  2. customevaporated in vacuo
  3. dry with materialThe ether phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe evaporation residue was purified by column chromatography on silica gel [toluene/acetone (20:1)]

Sources & evidence

ORD record
ord-b3f67891bee54941ae2fd8e9ae0d6fb6
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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